With Graham and Sophie away at Lance Bass Space Camp, Angie decides to spend the summer in Barstow with Derek, leaving Will plotting a way to stop her. Meanwhile, Rory and the twins attempt to make Poppy and Douglas jealous with the goal of getting them back together.

When Graham writes a letter to Santa asking for either a white Christmas or to meet his father, Angie goes on a mission to find snow in Southern California, with the help of Will and Sophie. Meanwhile, after Rory, Emma and Amy find out that Poppy and Douglas are romantically involved, the kids use this knowledge to their advantage to guilt their parents into buying them more Christmas presents.

Angie struggles to recall the events of a wine-filled night of packing with Will, while Poppy secretly encourages Will to share his true feelings. Meanwhile, Derek arrives to gather Angie and her belongings, while Rory and Miggy are enlisted to find a hot guy to sublet the house.

Angie attempts to help Poppy through her situation with Douglas, only to be confronted by the fact that she might have feelings for Derek again. Meanwhile, Will distracts himself from thinking about Angie by smothering Douglas with a little too much love and support, causing him to look for comfort in the last place he expected to find it.

After learning that Angie's ex Derek lives near Space Camp, Will convinces Angie to confront him about leaving her when she was pregnant, which results in a rowdy and awkward encounter between the three of them. Meanwhile, Poppy internally struggles with who she truly has romantic feelings for.

To celebrate Angie's 30th birthday, Will throws a big party recreating Ozzfest, which Angie missed in her 20s; but when Angie assumes Owen planned it for her, awkward encounters ensue. Meanwhile, Douglas takes Graham shopping to help him find the perfect gift for his mom, Angie, for her birthday, but a distracted Douglas results in Graham buying a not-so-on-point gift.

Struggling with unexpected news from Ron’s new wife, Sharon, Poppy uses an adventure with Angie to help distract herself from facing her emotions. Meanwhile, Sophie takes on Hilltop, protesting leaving Pete the parrot at school over the three-day weekend, causing Will and Douglas to clash over their stances on activism.

It's Valentine’s Day! Will and Angie have reunited to help run the student-parent dinner at Hilltop, where the kids are serving up questionable meals to paying customers. Meanwhile, Big Red is back in town and Douglas is worried about how Poppy will react.

Douglas discovers that Amy is a math genius and is overwhelmed with how much time he has to spend to treat his daughters as individuals for the first time ever; this eventually leads to Emma moving into their private shed to get some space from Amy. Meanwhile, Graham makes a new friend at school, causing Angie to have to spend time with his new friend's mom, Nora, to Angie's chagrin. After Angie meets Nora in person and enjoys spending time with her, Poppy starts to grow jealous of Angie's newfound friendship.

When Graham brings Douglas’ box of 1950s Playboy magazines for show and tell, Angie fears she is a bad mom and knows she has to give “the talk” to Graham. However, Graham has other plans and asks to hear about it from Will and Douglas, which brings out Will’s own insecurities when he discovers some kept secrets about his own father’s relationships. Meanwhile, Poppy tries to become closer with the twins by helping them discover their individual personalities.

In a magical encounter at the Bachelor mansion, Chris Harrison bestows his wisdom on a frustrated Poppy and Angie, attempting to restore their faith in love and happy endings. Meanwhile, Will saves one of the kids at school from playground injury; and Douglas insists Will capitalize on the glow from this heroic act by getting as much attention from women as possible within its 24-hour window.

After Angie decides it’s finally time for Graham to meet his dad, Dere, sickness overtakes the household. Derek is forced to either step in and help or head back out to his van. Meanwhile, when Sophie overhears some big news about Will and Tracy, she takes it upon herself to intervene; and the twins face their first professional failure.

When Sharon goes into labor, Poppy and the gang step up to help her get to the hospital, telling each of their own birth stories to help distract her from Ron’s absence.

Will works through a difficult situation after he learns something about Angie’s new boyfriend, Colin, that she won’t want to hear. Meanwhile, Poppy and Douglas struggle to see eye-to-eye about their future, and the kids are home alone for the first time with Graham in charge.

When Will's ex, Mia, shows up unexpectedly for Sophie's birthday, Will gets frustrated that she undermines his rules with Sophie. Angie tries to help Will cope by having a fun girls' night at her place and by giving some co-parenting advice, but Poppy reveals and Will quickly learns that Angie isn't the best advice giver. Meanwhile, inspired by Mia's humanitarian work, Miggy and Graham decide to give some items to charity but regret it immediately and seek out help from Douglas to get the items back.

Douglas is stuck hosting the kids' Saturday sleepover, and Will uses this as an opportunity to try to bond with Douglas, something he hasn't been able to do before. Angie and Graham both struggle with their own fear of sleepovers - Graham is worried to stay the night without his mom and not in his own house, and Angie is worried to sleep over with her man friend Owen. Meanwhile, Poppy helps Miggy come up with potential job ideas in order to help him become more responsible.

Douglas agrees to babysit the kids on Valentine's Day, but when Graham finds himself in a Valentine's Day emergency and Big Red shows up unannounced, Douglas and Big Red band together to help Graham. Meanwhile, Will and Miggy celebrate "Palentine's Day" together - a day honoring the love of two friends - but when they run into Angie at her second job, they help her finish her deliveries so she can be with Owen on Valentine's Day.

After seeing the way Douglas and the twins are barely affected by the death of their guinea pig, Pickle, Poppy encourages Douglas to stop repressing his and the twins' feelings. After seeing how close Graham and Will are becoming, Angie gets jealous when Graham asks Will to go get a colonoscopy to check on his health, so Angie decides to get one herself.

Will, a 30-something guy, has been so focused on raising his daughter that he’s lost sight of who he is as a man. When the other single parents see just how far down the rabbit hole of PTA, parenting and princesses Will has gone, they band together to get him out in the dating world and make him realize that being a great parent doesn’t mean sacrificing everything about your own identity.

Will wants to get back together with Mia, but as their relationship progresses, he finds himself having to choose between the "normal" family he's always wanted and the new family he's created with Angie, Poppy, Miggy, Douglas and the kids. In order to get Will to come back to his senses about Mia, Angie kicks him off the babysitting grid and fills the spot with Dr. Mark, Douglas' rival dermatologist, much to Douglas' chagrin. Meanwhile, Graham is nervous to compete in the talent show and relies on Will to calm him down when he gets nervous on stage.

When no one bids on "Lunch with KZOP's Will Cooper" at the school auction, Poppy and Sophie scheme together to recruit Dr. Biscuits to bid on Will and play the role of his No. 1 fan. Meanwhile, Douglas attempts to teach a reluctant Angie how to cut back on extra spending and become more fiscally responsible.

Will decides to audition for his dream job as an on-camera weatherman, but in order to succeed, he needs a little help from Miggy, Poppy and Sophie to hone in on the perfect persona. Meanwhile, after Angie discovers that Graham has the word "FARTS" written on his forehead in permanent marker, she goes on a mission to obtain an apology from the responsible parties - Emma and Amy - and unfortunately Douglas does not provide much help.

When Will gets busy cooking Thanksgiving dinner at Douglas’ home, he asks Angie to hang out with Tracy Freeze. Angie reluctantly does so, only to realize that Tracy is actually wonderful, except for a secret she’s keeping from Will. Meanwhile, Miggy shows up to Thanksgiving dinner with the kids’ teacher, Ms. Pronstroller, as his date, and he enlists Douglas’ assistance in helping them form an in-person connection, given all of their previous communication has been via texts, DMs and memes.

Will is crushed when Sophie wants to tone down Halloween and invites a boy over. Poppy and the twins attempt to convince a reluctant Douglas to wear a silly costume; after he finally puts it on, he meets the woman of his dreams, who he now is sure will not take him seriously. Meanwhile, Angie struggles to tell her boss that she needs to leave work to be with her son on Halloween, leaving Graham's costume in limbo.

When Poppy's ex-husband, Ron, gets serious with his latest girlfriend, Poppy has to deal with the reality of another woman helping to raise her kid. The secret gets out that Sophie has a crush on Graham, which causes a stir not only in the first-grade classroom, but also between Angie and Will. Meanwhile, Miggy gets cold feet after asking Douglas to remove his tattoo of Zara's initials, and Douglas has to help him realize that his relationship with Zara is officially over.

Will encourages Angie to rediscover her passion for heavy metal music by taking a guitar class, and in turn, Angie insists that Will get back in the field covering weather by driving both of them into a storm. Meanwhile, the rest of the gang explore their romantic passions as Douglas pursues his crush on Big Red with the help of Miggy, and Poppy feels an instant connection with a dreamy musician.

Will is thrilled to throw the first-grade parent social so that he can use this event to springboard his anti-smartphone platform to get parents to wait to buy their kids cellphones until eighth grade. He ropes his new love interest, Dr. Dewan, into helping him, but his plan doesn't work out quite like he had hoped. Douglas offers to have the social at his house so he can exact revenge on his rival dermatologist, Mark, whom Douglas is convinced stole his prized pen.

Angie uses Sophie as bait to get time with her crush Colin by setting up Sophie and Percy, Colin’s son, on a playdate at Angie’s house. Meanwhile, Poppy and Douglas navigate Douglas’ first night sleeping at Poppy’s house, which doesn’t go as expected; and Graham and Will go on a bro-date of their own to the pizza parlor.